Mar 5, 2025; Boston, Massachusetts, USA; Boston Celtics guard Derrick White (9) drives on Portland Trail Blazers guard Anfernee Simons (1) during the first quarter at TD Garden. Mandatory Credit: Winslow Townson-Imagn Images Winslow Townson-Imagn Images

Celtics' Trade Deadline Revolves Around One Player, Says Insider

Originally posted on Boston Celtics on SI | By Ryan Stano | Last updated Oct 7, 2025 1:10 PM ET

The Boston Celtics acquired Anfernee Simons in the offseason while they dumped Jrue Holiday to the Portland Trail Blazers. It was a move that was made with salary cap implications in mind.

Despite the Celtics' best efforts, they have not been able to reroute him to a different home. They will have him on the roster on opening night, even though he's owed $27.7 million this year.

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Simons will likely come off the bench for the Celtics this season. One insider believes that the trade deadline for the Celtics will revolve around him.

NBA insider believes Celtics' Trade deadline will revolve around Anfernee Simons

Bobby Marks of ESPN believes that how the Celtics deal with Anfernee Simons will determine how they approach the trade deadline this year.

"How Boston adds to its roster for the future -- or subtracts in the short term -- could come down to Anfernee Simons, whom the franchise acquired in the Holiday deal with Portland. Simons has a $27.7 million expiring contract," Marks writes.

Simons is a good player who can help a lot of teams offensively, but he fits a very specific kind of team that has players who can help him defensively. He's a smaller guard who struggles on that end.

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Marks notes that the Celtics are still in the luxury tax and a first-apron team, so that makes things tricky for them.

"Boston remains $12 million over the luxury tax, and is projected to pay a $39 million penalty," Marks adds. "The Celtics are also a first-apron team, and not allowed to take back more money in a trade."

The Celtics might stand pat at the trade deadline

Trading Simons at the trade deadline doesn't give them any luxury tax relief for this year. While he's an expiring contract, the Celtics would have to exactly match a salary to get rid of him.

It might make more sense for the Celtics to keep him all year so that his salary falls off the books once the season ends. From there, they can figure out where to allocate some money in free agency.

Last season with the Trail Blazers, Simons averaged 19.3 points, 2.7 rebounds, and 4.8 assists per game.